Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita–Baylis–Hillman Carbonates with Water
The Journal of Organic Chemistry2011Vol. 76(16), pp. 6894–6900
Citations Over TimeTop 12% of 2011 papers
Bo Zhu, Lin Yan, Yuanhang Pan, Richmond Lee, Hongjun Liu, Zhiqiang Han, Kuo‐Wei Huang, Choon‐Hong Tan, Zhiyong Jiang
Abstract
A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using (18)O-labeling experiments.
Related Papers
- → Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates(2015)668 cited
- → Metal-catalyzed rearrangements of allylic esters(1984)59 cited
- → One-Pot Synthesis of Homoallylic Alcohols via a Facile Conversion of Allylic Alcohols into Allylic Iodides(1989)30 cited
- → Facile synthesis of (E)-allylic alcohols by acid-catalyzed modification of the Mislow-Evans rearrangement of allylic sulfoxides.(1985)15 cited
- Synthesis and reactions of organic compounds with a nitrogen atom. Part XVI. Reactions of (-)-4-chloro-3(10)-carene and(+)-10-chloro-3-carene with phenyltelluro- andc phenylselenosodium(1999)